CN116724020A - Novel compound and organic light emitting device comprising the same - Google Patents
Novel compound and organic light emitting device comprising the same Download PDFInfo
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- CN116724020A CN116724020A CN202280010761.8A CN202280010761A CN116724020A CN 116724020 A CN116724020 A CN 116724020A CN 202280010761 A CN202280010761 A CN 202280010761A CN 116724020 A CN116724020 A CN 116724020A
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- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- MUGLENOZWVKNRY-UHFFFAOYSA-N furan-3-amine Chemical compound NC=1C=COC=1 MUGLENOZWVKNRY-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Abstract
The present application relates to a novel organic light emitting material and an organic light emitting device including the same.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2021-0153380 at 2021, 11 and 9 and korean patent application No. 10-2022-01395164 at 2022, 10 and 26, the entire contents of the disclosures of which are incorporated herein as part of the present specification.
The present application relates to novel compounds and organic light emitting devices comprising the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons transition to the ground state again.
As for the organic matter used for the organic light emitting device as described above, development of new materials is continuously demanded.
Prior art literature
Patent literature
(patent document 1) Korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present invention relates to a novel organic light emitting material and an organic light emitting device including the same.
Solution to the problem
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
x is a single bond, O or S,
R 1 and R is 2 Each independently is hydrogen; deuterium; a halogen group; a nitrile group; a silyl group; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O, S 2-60 A heteroaryl group, which is a group,
a is an integer of 0 to 3,
b is an integer of 0 to 4,
L 1 to L 3 Each independently is a single bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising any one or more selected from N, O, S 2-60 A heteroarylene group,
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O, S 2-60 Heteroaryl, and Ar 1 And Ar is a group 2 At least one of which is a substituent represented by the following chemical formula 2,
[ chemical formula 2]
In the above-mentioned chemical formula 2,
R 3 is hydrogen; a halogen group; a nitrile group; a silyl group; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O, S 2-60 A heteroaryl group, which is a group,
R 11 to R 14 Each independently is-CH 3 、-CH 2 D、-CHD 2 or-CD 3 ，
c is an integer of 0 to 7,
the silyl group refers to-Si (Z) 1 )(Z 2 )(Z 3 ) Here, Z 1 To Z 3 Each independently is a substituted or unsubstituted C 1-60 Alkyl, or substituted or unsubstituted C 6-60 Aryl groups.
In addition, the present invention provides an organic light emitting device, wherein comprising: a first electrode, a second electrode provided opposite to the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
Effects of the invention
The compound represented by the above chemical formula 1 may be used as a material of an organic layer of an organic light emitting device in which improvement of efficiency, lower driving voltage, and/or improvement of lifetime characteristics may be achieved. In particular, the compound represented by the above chemical formula 1 may be used as a material for hole injection, hole transport, light emission, electron transport, and/or electron injection.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 3, an electron injection and transport layer 8, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above hole transporting layer or the electron suppressing layer.
Detailed Description
In the following, the invention will be described in more detail in order to aid understanding thereof.
The present invention provides a compound represented by the above chemical formula 1.
In the present description of the invention,or->Represents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio groupArylthio->Alkylsulfonyl->Arylsulfonyl->A silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; or a substituent comprising N, O and 1 or more substituents in 1 or more heteroaryl groups in the S atom is substituted or unsubstituted, or a substituent bonded to 2 or more substituents in the above-exemplified substituents is substituted or unsubstituted. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the substituent may have the following structure, but is not limited thereto.
In the present specification, in the ester group, oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the substituent may be a substituent of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the substituent may have the following structure, but is not limited thereto.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but the present invention is not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms,may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as phenyl, biphenyl, and terphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, and the like,A group, a fluorenyl group, etc., but is not limited thereto.
In this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the fluorenyl group is substituted, it may be thatEtc. However, the present invention is not limited thereto.
In the present specification, the heteroaryl group is a heteroaryl group containing 1 or more of O, N, si and S as a hetero element, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heteroaryl group has 6 to 30 carbon atoms. According to one embodiment, the heteroaryl group has 6 to 20 carbon atoms. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like, Azolyl, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->Oxazolyl, benzimidazolyl, benzothiazolyl, and benzocarbazoleRadical, benzothienyl, dibenzothienyl, benzofuranyl, phenanthroline (phenanthrine), isolOxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present specification, the aryl groups in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group are the same as those exemplified for the aryl groups described above. In the present specification, the alkyl group in the aralkyl group, alkylaryl group, and alkylamino group is the same as the above-mentioned alkyl group. In this specification, the heteroaryl group in the heteroaryl amine may be as described above with respect to the heteroaryl group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-described examples of alkenyl groups. In this specification, arylene is a 2-valent group, and the above description of aryl can be applied in addition to this. In this specification, the heteroarylene group is a 2-valent group, and the above description of the heteroarylene group can be applied thereto. In this specification, the hydrocarbon ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the aryl group or cycloalkyl group can be applied. In this specification, the heteroaryl group is not a 1-valent group, but a combination of 2 substituents, and the above description of the heteroaryl group can be applied.
Preferably, R 1 And R is 2 Each independently may be hydrogen; deuterium; substituted or unsubstituted C 6-20 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O, S 2-20 Heteroaryl groups.
More preferably, R 1 And R is 2 Each independently can be hydrogen, deuterium, phenyl substituted with 1 or 2 tertiary butyl groups, biphenyl, naphthyl orR is as described above 1 And R is 2 Each phenyl, phenyl substituted by 1 or 2 tert-butyl, biphenyl, naphthyl or +.>In the case of phenyl, phenyl substituted by 1 or 2 tert-butyl groups, biphenyl, naphthyl orMay be unsubstituted or substituted with more than one deuterium.
Preferably L 1 To L 3 Each independently may be a single bond; substituted or unsubstituted C 6-20 Arylene groups; or substituted or unsubstituted C comprising any one or more selected from N, O, S 2-20 A heteroarylene group,
more preferably L 1 To L 3 Each independently may be a single bond, phenylene, or phenylene substituted with 4 deuterium.
Preferably Ar 1 And Ar is a group 2 Each independently is a substituted or unsubstituted C 6-20 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O, S 2-20 Heteroaryl, and Ar 1 And Ar is a group 2 At least one of them may be a substituent represented by the following chemical formula 2,
[ chemical formula 2]
More preferably, ar as described above 1 And Ar is a group 2 R of chemical formula 2 3 And is hydrogen or deuterium, c may be an integer from 0 to 7.
More preferably Ar 1 And Ar is a group 2 Each independently is phenyl, phenyl substituted with 1 tert-butyl, phenyl substituted with 1 adamantyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl orAr as described above 1 And Ar is a group 2 Can be used forUnsubstituted or substituted by more than one deuterium, and Ar 1 And Ar is a group 2 At least one of which may be unsubstituted or substituted with more than one deuterium
Most preferably Ar 1 And Ar is a group 2 Each independently is any one selected from the group consisting of 1 And Ar is a group 2 At least one of them may be
Preferably, the substituent represented by the above chemical formula 2 may be any one selected from the group consisting of:
preferably, R 11 To R 14 Each may be-CH 3 。
Representative examples of the compounds represented by the above chemical formula 1 are shown below:
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as an example, the compound represented by the above chemical formula 1 may be produced by the production method shown in the following chemical formula 1, and other compounds than these may be similarly produced.
[ reaction type 1]
In the above reaction scheme 1, X, R 1 、R 2 、a、b、L 1 To L 3 、Ar 1 And Ar is a group 2 As defined in chemical formula 1 above, Z is halogen, preferably Z is chlorine or bromine.
The amine substitution reaction of the above reaction formula 1 is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used for the amine substitution reaction may be modified according to a technique known in the art. The above-described production method can be more specifically described in the production example described later.
In addition, the present invention provides an organic light emitting device including the compound represented by the above chemical formula 1. As one example, the present invention provides an organic light emitting device, including: a first electrode, a second electrode provided opposite to the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure or a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as the organic layer. However, the structure of the organic light emitting device is not limited thereto, and may include a greater or lesser number of organic layers.
The organic layer may include a hole transporting layer, a hole injecting layer, a layer that performs hole transport and hole injection simultaneously, or an electron suppressing layer, and the hole transporting layer, the hole injecting layer, the layer that performs hole transport and hole injection simultaneously, or the electron suppressing layer may include a compound represented by chemical formula 1.
In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure of an organic light emitting device according to an embodiment of the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above light emitting layer.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 3, an electron injection and transport layer 8, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above hole transporting layer or the electron suppressing layer.
The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that 1 or more of the organic layers contain the compound represented by chemical formula 1. In addition, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be manufactured as follows: PVD (physical Vapor Deposition) process such as sputtering (sputtering) or electron beam evaporation (physical vapor deposition) is used to vapor-deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
In addition, the compound represented by the above chemical formula 1 may be used not only in a vacuum deposition method but also in a solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
As an example, the first electrode may be an anode, the second electrode may be a cathode, or the first electrode may be a cathode, and the second electrode may be an anode.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that injects holes from an electrode, and the following compounds are preferable as the hole injection substance: a compound which has a hole transporting ability, has an effect of injecting holes from the anode, has an excellent hole injecting effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from migrating to the electron injecting layer or the electron injecting material, and has an excellent thin film forming ability. The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and a hole-transporting substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer is preferable, and a substance having a large mobility to the holes is preferable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions. Preferably, the compound represented by the above chemical formula 1 may be used as the hole transport layer substance.
In the present invention, the "hole injection and transport layer" is a layer that functions as both the hole injection layer and the hole transport layer, and the materials that function as the layers may be used singly or in combination.
The electron suppression layer is a layer which is interposed between the hole transport layer and the light emitting layer, and is also called an electron blocking layer, in order to prevent electrons injected from the cathode from being transferred to the hole transport layer without recombination in the light emitting layer. The electron-inhibiting layer is preferably a substance having a smaller electron affinity than the electron-transporting layer. Preferably, the compound represented by the above chemical formula 1 may be used as the electron-inhibiting layer substance.
The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and preferably has high quantum efficiency for fluorescence or phosphorescence. Specifically, there are 8-hydroxyquinoline aluminum complex (Alq 3 ) A carbazole-based compound, a dimeric styryl (dimerized styryl) compound; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
Above hairThe optical layer may comprise a host material and a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compoundsPyrimidine derivatives, etc., but are not limited thereto.
Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group, Bisindenopyrene, and the like, and a styrylamine compound is a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can well receive electrons from the cathode and transfer the electrons to the light emitting layer, and is suitable for a substance having high mobility of electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The electron transport layer may be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materialsThe sub-component is a general substance having a low work function accompanied by an aluminum layer or a silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.
The electron injection layer is a layer that injects electrons from an electrode, and preferably is a compound as follows: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole injection layer, and has excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,/->The diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and the like, and their derivatives, metal complexes, and nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
In the present invention, the "electron injection and transport layer" is a layer that functions as both the electron injection layer and the electron transport layer, and the materials that function as the respective layers may be used singly or in combination, but the present invention is not limited thereto.
The organic light emitting device according to the present invention may be a bottom emission (bottom emission) device, a top emission (top emission) device, or a bi-directional light emitting device, and in particular, may be a bottom emission device requiring relatively high light emitting efficiency.
In addition, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
The production of the compound represented by the above chemical formula 1 and the organic light emitting device including the same is specifically illustrated in the following examples. However, the following examples are given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
Synthesis example
Synthesis example 1 Synthesis of Compound 1
In 2 '-bromospiro [ adamantane-2, 9' -fluorene](20.0 g,54.75 mmol) and N- ([ 1,1' -biphenyl)]To (4-yl) -5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine (19.85 g,55.84 mmol) and sodium t-butoxide (7.37 g,76.65 mmol) were added toluene (300 ml), and then heated and stirred for 10 minutes. To the above mixture was added bis (tri-t-butylphosphine) palladium (0.14 g,0.27 mmol) dissolved in toluene (30 ml), followed by stirring with heating for 1 hour. After completion of the reaction and filtration, the layers were separated with toluene and water. After the solvent was removed, it was recrystallized from ethyl acetate, whereby the above-mentioned compound 1 (27.5 g, yield 78.49%) was obtained. (MS: [ M+H ] ] + ＝640)
Synthesis example 2 Synthesis of Compound 2
Using 2 '-bromospiro [ adamantane-2, 9' -fluorene](20.0 g,54.75 mmol) and 5, 8-tetramethyl-N- (4- (naphthalen-1-yl) phenyl) -5,6,7, 8-tetrahydronaphthalen-2-amine (22.65 g,55.84 mmol), the above-mentioned compound 2 (29.5 g, yield 78.09%) was obtained by the same method as in the above-mentioned synthetic example 1. (MS: [ M+H ]] + ＝690)
Synthesis example 3 Synthesis of Compound 3
Using 2 '-bromospiro [ adamantane-2, 9' -fluorene](20.0 g,54.75 mmol) and 9, 9-dimethyl-N- (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) -9H-fluoren-2-amine (22.09 g,55.84 mmol), the above-mentioned compound 3 (28.5 g, yield 76.55%) was obtained by the same method as in the above-mentioned synthetic example 1. (MS: [ M+H ]] + ＝680)
Synthesis example 4 Synthesis of Compound 4
Using 2 '-bromospiro [ adamantane-2, 9' -fluorene](20.0 g,54.75 mmol) and N- (4- (t-butyl) phenyl) -5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine (19.85 g,55.84 mmol), the above-mentioned compound 4 (26.5 g, yield 78.08%) was obtained by the same method as in the above-mentioned synthetic example 1. (MS: [ M+H ]] + ＝620)
Synthesis example 5 Synthesis of Compound 5
Using 2 '-bromospiro [ adamantane-2, 9' -fluorene](20.0 g,54.75 mmol) and N- (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) dibenzo [ b, d ] ]Furan-3-amine (20.63 g,55.84 mmol) the above compound 5 (28.0 g, yield 78.21%) was obtained by the same method as in the above synthesis example 1. (MS: [ M+H ]] + ＝654)
Synthesis example 6 Synthesis of Compound 6
Using 2 '-bromospiro [ adamantane-2, 9' -fluorene](20.0 g,54.75 mmol) and bis (5, 8-tetramethyl-5, 6,7, 8-tetralinHydronaphthalen-2-yl) amine (21.76 g,55.84 mmol), the above-mentioned compound 6 (29.0 g, yield 78.58%) was obtained by the same method as in the above-mentioned synthetic example 1. (MS: [ M+H ]] + ＝674)
Synthesis example 7 Synthesis of Compound 7
Using 2 '-bromospiro [ adamantane-2, 9' -fluorene](20.0 g,54.75 mmol) and N- (4- (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) phenyl) - [1,1' -biphenyl ]]4-amine (24.10 g,55.84 mmol), compound 7 (30.5 g, yield 77.80%) was obtained by the same method as in Synthesis example 1. (MS: [ M+H ]] + ＝716)
Synthesis example 8 Synthesis of Compound 8
Using 2'- (4-chlorophenyl) spiro [ adamantane-2, 9' -fluorene](20.0 g,50.38 mmol) and N- ([ 1,1' -biphenyl)]-4-yl) -5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine (18.27 g,51.39 mmol), the above-mentioned compound 8 (28.5 g, yield 79.01%) was obtained by the same method as in the above-mentioned synthesis example 1. (MS: [ M+H ] ] + ＝716)
Synthesis example 9 Synthesis of Compound 9
Using 2'- (4-chlorophenyl) spiro [ adamantane-2, 9' -fluorene](20.0 g,50.38 mmol) and bis (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine (20.02 g,51.39 mmol), the above-mentioned compound 9 (30.0 g, yield 79.38%) was obtained by the same method as in the above-mentioned synthetic example 1. (MS: [ M+H ]] + ＝750)
Synthesis example 10 Synthesis of Compound 10
Using 2 '-bromospiro [ adamantane-2, 9' -fluorene](20.0 g,54.75 mmol) and N- ([ 1,1' -biphenyl)]-4-yl) -5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-1-amine (19.85 g,55.84 mmol), the above-mentioned compound 10 (27.5 g, yield 78.49%) was obtained by the same method as in the above-mentioned synthesis example 1. (MS: [ M+H ]] + ＝640)
Synthesis example 11 Synthesis of Compound 11
Using 2 '-bromospiro [ adamantane-2, 9' -fluorene](20.0 g,54.75 mmol) and bis (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-1-yl) amine (21.76 g,55.84 mmol), the above-mentioned compound 11 (28.5 g, yield 77.23%) was obtained by the same method as in the above-mentioned synthetic example 1. (MS: [ M+H ]] + ＝674)
Synthesis example 12 Synthesis of Compound 12
By means of 4 '-bromospiro [ adamantane-2, 9' -fluorene](20.0 g,54.75 mmol) and bis (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-1-yl) amine (21.76 g,55.84 mmol), the above-mentioned compound 12 (28.5 g, yield 77.23%) was obtained by the same method as in the above-mentioned synthetic example 1. (MS: [ M+H ] ] + ＝674)
Synthesis example 13 Synthesis of Compound 13
By means of 4 '-bromospiro [ adamantane-2, 9' -fluorene](20.0 g,54.75 mmol) and N- ([ 1,1' -biphenyl)]-4-yl) -5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine (19.85 g,55.84 mmol),the above compound 13 (27.5 g, yield 78.49%) was obtained by the same method as in the above synthetic example 1. (MS: [ M+H ]] + ＝640)
Synthesis example 14 Synthesis of Compound 14
By means of 4 '-bromospiro [ adamantane-2, 9' -fluorene](20.0 g,54.75 mmol) and bis (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine (21.76 g,55.84 mmol), the above-mentioned compound 14 (29.0 g, yield 78.58%) was obtained by the same method as in the above-mentioned synthetic example 1. (MS: [ M+H ]] + ＝674)
Synthesis example 15 Synthesis of Compound 15
Using 3 '-bromospiro [ adamantane-2, 9' -fluorene](20.0 g,54.75 mmol) and N- ([ 1,1' -biphenyl)]-4-yl) -5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine (19.85 g,55.84 mmol), the above-mentioned compound 15 (27.0 g, yield 77.06%) was obtained by the same method as in the above-mentioned synthesis example 1. (MS: [ M+H ]] + ＝640)
Synthesis example 16 Synthesis of Compound 16
Using 3 '-bromospiro [ adamantane-2, 9' -fluorene](20.0 g,54.75 mmol) and bis (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine (21.76 g,55.84 mmol), the above-mentioned compound 16 (28.5 g, yield 77.23%) was obtained by the same method as in the above-mentioned synthetic example 1. (MS: [ M+H ] ] + ＝674)
Synthesis example 17 Synthesis of Compound 17
Using 2 '-bromospiro [ adamantane-2, 9' -xanthenes](20.0 g,52.45 mmol) and N- ([ 1,1' -biphenyl)]-4-yl) -5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine (19.02 g,53.50 mmol) the above-mentioned compound 17 (27.0 g, yield 78.48%) was obtained by the same method as in the above-mentioned synthesis example 1. (MS: [ M+H ]] + ＝656)
Synthesis example 18 Synthesis of Compound 18
Using 2 '-bromospiro [ adamantane-2, 9' -xanthenes](20.0 g,52.45 mmol) and bis (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine (20.85 g,53.50 mmol), the above-mentioned compound 18 (28.5 g, yield 78.75%) was obtained by the same method as in the above-mentioned synthetic example 1. (MS: [ M+H ]] + ＝690)
Synthesis example 19 Synthesis of Compound 19
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Using 3 '-bromospiro [ adamantane-2, 9' -xanthenes](20.0 g,52.45 mmol) and N- ([ 1,1' -biphenyl)]-4-yl) -5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine (19.02 g,53.50 mmol) the above-mentioned compound 19 (27.0 g, yield 78.48%) was obtained by the same method as in the above-mentioned synthesis example 1. (MS: [ M+H ]] + ＝656)
Synthesis example 20 Synthesis of Compound 20
Using 3 '-bromospiro [ adamantane-2, 9' -xanthenes](20.0 g,52.45 mmol) and bis (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine (20.85 g,53.50 mmol), the above-mentioned compound 20 (28) was obtained by the same method as in the above-mentioned Synthesis example 1 5g, 78.75% yield). (MS: [ M+H ]] + ＝690)
Synthesis example 21 Synthesis of Compound 21
Using 4 '-bromospiro [ adamantane-2, 9' -xanthene](20.0 g,52.45 mmol) and N- ([ 1,1' -biphenyl)]-4-yl) -5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine (19.02 g,53.50 mmol) the above compound 21 (26.5 g, yield 77.03%) was obtained by the same method as in the above synthesis example 1. (MS: [ M+H ]] + ＝656)
Synthesis example 22 Synthesis of Compound 22
Using 4 '-bromospiro [ adamantane-2, 9' -xanthene](20.0 g,52.45 mmol) and bis (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine (20.85 g,53.50 mmol), the above-mentioned compound 22 (28.0 g, yield 77.37%) was obtained by the same method as in the above-mentioned synthetic example 1. (MS: [ M+H ]] + ＝690)
Synthesis example 23 Synthesis of Compound 23
By means of 2 '-bromospiro [ adamantane-2, 9' -thioxanthenes](20.0 g,50.33 mmol) and N- ([ 1,1' -biphenyl)]-4-yl) -5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine (18.25 g,51.34 mmol) the above-mentioned compound 23 (26.5 g, yield 78.35%) was obtained by the same method as in the above-mentioned synthesis example 1. (MS: [ M+H ]] + ＝672)
Synthesis example 24 Synthesis of Compound 24
By means of 2 '-bromospiro [ adamantane-2, 9' -thioxanthenes](20.0 g,50.33 mmol) and bis (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine (20.00 g,51.34 mmol), the above-mentioned compound 24 (28.0 g, yield 78.79%) was obtained by the same method as in the above-mentioned synthetic example 1. (MS: [ M+H ] ] + ＝706)
Synthesis example 25 Synthesis of Compound 25
By 3 '-bromospiro [ adamantane-2, 9' -thioxanthenes](20.0 g,50.33 mmol) and N- ([ 1,1' -biphenyl)]-4-yl) -5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine (18.25 g,51.34 mmol) the above-mentioned compound 25 (26.5 g, yield 78.35%) was obtained by the same method as in the above-mentioned synthesis example 1. (MS: [ M+H ]] + ＝672)
Synthesis example 26 Synthesis of Compound 26
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By 3 '-bromospiro [ adamantane-2, 9' -thioxanthenes](20.0 g,50.33 mmol) and bis (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine (20.00 g,51.34 mmol), the above-mentioned compound 26 (28.0 g, yield 78.79%) was obtained by the same method as in the above-mentioned synthetic example 1. (MS: [ M+H ]] + ＝706)
Synthesis example 27 Synthesis of Compound 27
Using 5' -chloro-2 ' -phenylspiro [ adamantane-2, 9' -fluorene](20.0 g,50.38 mmol) and N- ([ 1,1' -biphenyl)]-4-yl) -5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine (18.27 g,51.39 mmol) the above-mentioned compound 27 (28.5 g, yield 79.01%) was obtained by the same method as in the above-mentioned synthesis example 1. (MS: [ M ]+H] + ＝716)
Synthesis example 28 Synthesis of Compound 28
Using 2' -chloro-4 ' -phenylspiro [ adamantane-2, 9' -fluorene](20.0 g,50.38 mmol) and 9, 9-dimethyl-N- (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) -9H-fluoren-2-amine (20.33 g,51.39 mmol), the above-mentioned compound 28 (30.0 g, yield 78.76%) was obtained by the same method as in the above-mentioned synthetic example 1. (MS: [ M+H ] ] + ＝756)
Synthesis example 29 Synthesis of Compound 29
Using 2' -chloro-7 ' -phenylspiro [ adamantane-2, 9' -fluorene](20.0 g,50.38 mmol) and 9, 9-dimethyl-N- (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) -9H-fluoren-2-amine (20.33 g,51.39 mmol), the above-mentioned compound 29 (30.5 g, yield 80.01%) was obtained by the same method as in the above-mentioned synthetic example 1. (MS: [ M+H ]] + ＝756)
Synthesis example 30 Synthesis of Compound 30
Using 2' - (4- (tert-butyl) phenyl) -7' -chlorospiro [ adamantane-2, 9' -fluorene](20.0 g,44.14 mmol) and 9, 9-dimethyl-N- (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) -9H-fluoren-2-amine (17.81 g,45.03 mmol), the above-mentioned compound 30 (28.5 g, yield 79.50%) was obtained by the same method as in the above-mentioned synthetic example 1. (MS: [ M+H ]] + ＝812)
Synthesis example 31 Synthesis of Compound 31
By N- ([ 1,1' -biphenyl)]-4-yl) -3 '-phenylspiro [ adamantan-2, 9' -fluorene]-2' -amine (20.0 g,37.76 mmol) and 6-bromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (10.29 g,38.51 mmol), the above compound 31 (21.0 g, yield 77.67%) was obtained by the same method as in the above synthesis example 1. (MS: [ M+H ]] + ＝716)
Synthesis example 32 Synthesis of Compound 32
Using 3'- (4- (tert-butyl) phenyl) -N- (9, 9-dimethyl-9H-fluoren-2-yl) spiro [ adamantan-2, 9' -fluorene ]-2' -amine (20.0 g,31.95 mmol) and 6-bromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (8.71 g,32.59 mmol), the above-mentioned compound 32 (20.0 g, yield 77.07%) was obtained by the same method as in the above-mentioned synthetic example 1. (MS: [ M+H ]] + ＝812)
Synthesis example 33 Synthesis of Compound 33
By N- ([ 1,1' -biphenyl)]-4-yl) -3 '-phenylspiro [ adamantan-2, 9' -fluorene]-4' -amine (20.0 g,37.76 mmol) and 6-bromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (10.29 g,38.51 mmol), the above-mentioned compound 33 (20.5 g, yield 75.82%) was obtained by the same method as in the above-mentioned synthetic example 1. (MS: [ M+H ]] + ＝716)
Synthesis example 34 Synthesis of Compound 34
In 3 '-phenylspiro [ adamantane-2, 9' -fluorene]-2' -amine (15.0 g,39.73 mmol) and 6-bromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (21.76 g,81.45 mmol),And sodium t-butoxide (10.69 g,111.24 mmol) to which xylene (300 m 1) was added, followed by stirring with heating for 10 minutes. To the above mixture was added bis (tri-t-butylphosphine) palladium (0.10 g,0.20 mmol) dissolved in xylene (30 ml), followed by stirring with heating for 1 hour. After completion of the reaction and filtration, the layers were separated with xylene and water. After the solvent was removed, it was recrystallized from ethyl acetate, whereby the above-mentioned compound 34 (23.5 g, yield 78.85%) was obtained. (MS: [ M+H ] ] + ＝750)
< example >
Example 1-1
ITO (Indium Tin Oxide) toThe glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, the following compound HAT was usedAnd performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, as a hole transport layer, the following compound HT1 was used as a hole transport layer>After vacuum evaporation, the compound 1 produced in synthesis example 1 was treated with +.>Is subjected to thermal vacuum evaporation. Next, as a light-emitting layer, the following compound BH and the following compound BD were added in a weight ratio of 25:1, in +. >Vacuum evaporation was performed on the thickness of (c). Next, as a hole-suppressing layer, the following compound HB1 was used as +.>Vacuum evaporation was performed on the thickness of (c). Next, as a layer in which electron transport and electron injection are performed simultaneously, the following compound ET1 and the following compound Liq are given as 1:1 in weight ratio of->Is subjected to thermal vacuum evaporation. On the electron transport and electron injection layer, lithium fluoride (LiF) is added in sequence +.>Is made of aluminum +.>And vapor deposition is performed to form a cathode, thereby manufacturing an organic light-emitting device.
Examples 1-2 to 1-20 and comparative examples 1-1 to 1-4
Organic light-emitting devices of examples 1-2 to 1-20 and comparative examples 1-1 to 1-4 were fabricated in the same manner as in example 1-1 described above, except that the compound described in table 1 below was used instead of compound 1. The structures of the compounds EB1 to EB4 used in comparative examples 1-1 to 1-4 are shown below.
Experimental example 1 ]
10mA/cm was applied to the organic light emitting devices fabricated in examples 1-1 to 1-20 and comparative examples 1-1 to 1-4 2 The voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in table 1 below. On the other hand, T95 refers to the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.
TABLE 1
As shown in table 1 above, it was confirmed that the compound of the present invention has excellent electron inhibitory ability, and an organic light emitting device using it as an electron inhibitory layer shows remarkable effects in terms of driving voltage, efficiency and lifetime.
Examples 2-1 to 2-27 and comparative examples 2-1 to 2-5
Organic light-emitting devices of examples 2-1 to 2-27 and comparative examples 2-1 to 2-5 were fabricated in the same manner as in example 1-1 except that the above compound EB1 was used as the electron-inhibiting layer and the compound HT1 described in table 2 below was used as the hole-transporting layer. The structures of the compounds HT2 through HT6 used in comparative examples 2-1 through 2-5 are shown below.
Experimental example 2
When a current of 10mA/cm2 was applied to the organic light emitting devices fabricated in examples 2-1 to 2-27 and comparative examples 1-1, 2-1 to 2-5, the voltage, efficiency, color coordinates and life were measured, and the results thereof are shown in Table 2 below. On the other hand, T95 refers to the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.
TABLE 2
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As shown in table 2 above, it was confirmed that the compound of the present invention has excellent hole transporting ability, and an organic light emitting device using it as a hole transporting layer shows remarkable effects in terms of driving voltage, efficiency and lifetime.
[ description of the symbols ]
1: substrate 2: anode
3: light emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: electron suppression layer 8: electron injection and transport layers.
Claims (9)
1. A compound represented by the following chemical formula 1:
[ chemical formula 1]
In the chemical formula 1 described above, a compound having the formula,
x is a single bond, O or S,
R 1 and R is 2 Each independently is hydrogen; deuterium; a halogen group; a nitrile group; a silyl group; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O, S 2-60 A heteroaryl group, which is a group,
a is an integer of 0 to 3,
b is an integer of 0 to 4,
L 1 to L 3 Each independently is a single bond; substituted or unsubstituted C 6-60 Arylene groups; or substituted or unsubstituted C comprising any one or more selected from N, O, S 2-60 A heteroarylene group,
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O, S 2-60 Heteroaryl, and Ar 1 And Ar is a group 2 At least one of which is a substituent represented by the following chemical formula 2,
[ chemical formula 2]
In the chemical formula 2 described above, the chemical formula,
R 3 deuterium; a halogen group; a nitrile group; a silyl group; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O, S 2-60 A heteroaryl group, which is a group,
R 11 to R 14 Each independently is-CH 3 、-CH 2 D、-CHD 2 or-CD 3 ，
c is an integer of 0 to 7,
the silyl group refers to-Si (Z) 1 )(Z 2 )(Z 3 ) Wherein Z is 1 To Z 3 Each independently is a substituted or unsubstituted C 1-60 Alkyl, or substituted or unsubstituted C 6-60 Aryl groups.
2. The compound of claim 1, wherein R 1 And R is 2 Each independently is hydrogen, deuterium, phenyl substituted with 1 or 2 tertiary butyl groups, biphenyl, naphthyl or
The R is 1 And R is 2 Each phenyl, phenyl substituted by 1 or 2 tert-butyl groups, biphenyl, naphthyl orWhen the phenyl groups are 1 or2 tert-butyl-substituted phenyl, biphenyl, naphthyl or +.>Unsubstituted or substituted with more than one deuterium.
3. The compound of claim 1, wherein L 1 To L 3 Each independently is a single bond, phenylene, or phenylene substituted with 4 deuterium.
4. The compound of claim 1, wherein Ar 1 And Ar is a group 2 Each independently is phenyl, phenyl substituted with 1 tert-butyl, phenyl substituted with 1 adamantyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl or The Ar is as follows 1 And Ar is a group 2 Unsubstituted or substituted with more than one deuterium,
Ar 1 and Ar is a group 2 At least one of which is unsubstituted or substituted by more than one deuterium
5. The compound according to claim 1, wherein the substituent represented by the chemical formula 2 is any one selected from the group consisting of:
6. the compound of claim 1, wherein Ar 1 And Ar is a group 2 Each independently is selected fromAny one of the group consisting of:
and
Ar 1 and Ar is a group 2 At least one of is
7. The compound according to claim 1, wherein the compound represented by chemical formula 1 is any one selected from the group consisting of:
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8. an organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 7.
9. The organic light-emitting device according to claim 8, wherein the organic layer is an electron-suppressing layer or a hole-transporting layer.
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| KR10-2021-0153380 | 2021-11-09 | ||
| KR10-2022-0139164 | 2022-10-26 | ||
| KR1020220139164A KR20230068301A (en) | 2021-11-09 | 2022-10-26 | Novel compound and organic light emitting device comprising the same |
| PCT/KR2022/016798 WO2023085670A1 (en) | 2021-11-09 | 2022-10-31 | Novel compound and organic light-emitting device comprising same |
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| CN116724020A true CN116724020A (en) | 2023-09-08 |
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